Title: Synthesis, Structure, and Biological Activity of des-Side Chain Analogues of 1alpha,25-Dihydroxyvitamin D(3) with Substituents at C18
Authors: Verlinden, Lieve
Verstuyf, Annemieke
Eelen, Guy
Bouillon, Roger
Ordóñez-Morán, Paloma
Larriba, María Jesús
Muñoz, Alberto
Rochel, Natacha
Sato, Yoshiteru
Moras, Dino
Maestro, Miguel
Seoane, Samuel
Dominguez, Fernando
Eduardo-Canosa, Silvina
Nicoletti, Daniel
Moman, Edelmiro
Mouriño, Antonio # ×
Issue Date: May-2011
Publisher: Wiley - V C H Verlag GmbH & Co. KGaA
Series Title: ChemMedChem vol:6 issue:5 pages:788-793
Abstract: An improved synthetic route to 1α,25-dihydroxyvitamin D(3) des-side chain analogues 2 a and 2 b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF-7 breast cancer cells and prodifferentiation activity toward SW480-ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitamin D receptor (hVDR) complexed to one of these analogues, 20(17→18)-abeo-1α,25-dihydroxy-22-homo-21-norvitamin D(3) (2 a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25-dihydroxyvitamin D(3) .
ISSN: 1860-7179
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Clinical and Experimental Endocrinology
× corresponding author
# (joint) last author

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